Cu-Catalyzed cis-selective ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent

Bowen Liu; Guochun Peng; Yu Zhang; Chunhui Liu; Jinbo Zhao

doi:10.1039/d0ob02557g

Cu-Catalyzed cis-selective ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent

Org Biomol Chem. 2021 Feb 25;19(7):1493-1497. doi: 10.1039/d0ob02557g.

Authors

Bowen Liu¹, Guochun Peng², Yu Zhang², Chunhui Liu³, Jinbo Zhao¹

Affiliations

¹ Department of Chemistry and Biology, Changchun University of Technology, Changchun, Jilin 130012, P. R. China. zhaojinbo@ccut.edu.cn.
² Key Laboratory of Functional Molecule Design and Synthesis of Jilin Province, Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, P. R. China.
³ College of Chemical and Materials Engineering, Xuchang University, Xuchang, Henan 461000, P. R. China and College of Chemistry and Institute of Green Catalysis, Zhengzhou Univeristy, Zhengzhou, Henan 450001, P. R. China.

PMID: 33527952
DOI: 10.1039/d0ob02557g

Abstract

The Cu(i)-catalyzed ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent provides access to cis-2-aryl-1,2-dihydronaphthalen-1-ol derivatives, in contrast to the exclusive trans-selectivity in related Cu-catalyzed reactions with Grignard reagents. DFT calculations suggest that the reaction possibly proceeds via boronic ester by-product assisted ring-opening as an alternative pathway to the canonical β-oxygen elimination as the rate-determining step.

Publication types

Research Support, Non-U.S. Gov't